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Sonic i think would have a much better relationship with bowser than with Eggman and while he would stop him here n there he would prob think Bowser has the chance of turning goodI always wondered if Bowser would be considered a bad guy by Sonic or not. Because when it comes to his goal of kidnapping Princess Peach and conquering the Mushroom Kingdom: yeah, there's no excuses there.
But I wonder how Sonic would react to Bowser being someone who genuinely cares about and is protective of his minions, is a genuinely good dad to his several adopted children and biological son, and, from what I've heard happens in Brothership, offers up protection and food to those who are loyal to his army.
tho depends how evil is Bowser at his peak